Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles

Weber L, Schnieder M, Lönnecke P (2001)
Journal of the Chemical Society. Dalton Transactions (23): 3459-3464.

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Abstract
The reduction of 2-bromo-1,3,2-diazaborole tBuNCH=CH(tBu)BBr (4c) with a potassium mirror in 1,2-dimethoxyethane afforded a non-separable 1 : 2 : 1 mixture of the compounds tBuNCH=CHN(tBu)BH (5), tBuNCH=CHN(tBu)BOCH3 (6) and {tBuNCH=CHN(tBu)B}(2)O (7). Reaction of 4c with a potassium-sodium alloy in N,N,N',N'-tetramethylethylenediamine led to 5 as the major product. 1,3,2-Diazaboroles tBuNCH=CHN(tBu)BN-Me-2 (8) and {tBuNCH=CHN(tBu)B}(2) (9) were spectroscopically identified as minor products. The treatment of 4c with potassium-sodium alloy in toluene solution in the presence of [15]crown-5 yielded a 1 : 1 mixture of 5 and the benzyl derivative tBuNCH=CHN( tBu)BCH2Ph (12). The same reaction in toluene-d(8) produced the deuterated species 5-d(1) and 12-d(7). tBuNCH=CHN(tBu)BCH3 (17) and 1,4-diazabutadiene (tBuN=CH)(2) (18) resulted from the treatment of tBuNCH=CHN(tBu)BSCH3 (15) with potassium-sodium alloy in n-hexane. In contrast to this, compound 9 was obtained as the main product of the reduction of tBuNCH=CHN(tBu)BStBu (16) under similar conditions. The reduction of the 1-bromo-2-tert-butyl-1,2-dihydro[1,3,2]diazaborolo[1,5-a]pyridine (19) smoothly produced the respective diborane(4) derivative (20) which was subjected to X-ray diffraction analysis.
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Weber L, Schnieder M, Lönnecke P. Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions. 2001;(23):3459-3464.
Weber, L., Schnieder, M., & Lönnecke, P. (2001). Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions(23), 3459-3464.
Weber, L., Schnieder, M., and Lönnecke, P. (2001). Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions, 3459-3464.
Weber, L., Schnieder, M., & Lönnecke, P., 2001. Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions, (23), p 3459-3464.
L. Weber, M. Schnieder, and P. Lönnecke, “Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles”, Journal of the Chemical Society. Dalton Transactions, 2001, pp. 3459-3464.
Weber, L., Schnieder, M., Lönnecke, P.: Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles. Journal of the Chemical Society. Dalton Transactions. 3459-3464 (2001).
Weber, Lothar, Schnieder, M., and Lönnecke, Peter. “Alkali metal reduction of 2-halogeno- and 2-thiolato-2,3-dihydro-1H-1,3,2-diazaboroles”. Journal of the Chemical Society. Dalton Transactions 23 (2001): 3459-3464.
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